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Water → 1-{1-[2,4-Bis(trifluoromethyl)phenyl]ethyl}piperidine-4-carbaldehyde

HRID 1620555
Notes
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Reaction equation

HRID 1620555 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[CH:13]([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][OH:22])[CH2:17][CH2:16]1)[CH3:14].C(N(CC)CC)C.O>CS(C)=O>[F:23][C:2]([F:1])([F:24])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[CH:13]([N:15]1[CH2:16][CH2:17][CH:18]([CH:21]=[O:22])[CH2:19][CH2:20]1)[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 86678735(1-{1-[2,4-Bis(trifluoromethyl)phenyl]ethyl}piperidin-4-yl)methanol

Product 1

HCID 866787361-{1-[2,4-Bis(trifluoromethyl)phenyl]ethyl}piperidine-4-carbaldehydeYield 57.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (1-{1-[2,4-bis(trifluoromethyl)phenyl]ethyl}piperidin-4-yl)methanol (2.0 g) and triethylamine (2.35 mL) in DMSO (22.5 mL) was added sulfur trioxide pyridine complex (2.69 g). The reaction mixture was stirred at room temperature for 1.5 hr, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by so silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.15 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by so silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0e5f134be38c4e889ebdb4718c810bbd
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772277B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes